4-Methylmorpholine → HCID 131735115, compound

HRID 929301Notes

Reaction equation

HRID 929301 reaction equation
[Cl:1][C:2]1[C:6]([NH:7][CH3:8])=[CH:5][N:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1.[C:15]([O:19][C:20]([NH:22][C@@H:23]1[CH2:27][CH2:26][C@H:25]([C:28]([OH:30])=O)[CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CN1CCOCC1>CN(C=O)C.CCOC(C)=O.O>[C:15]([O:19][C:20](=[O:21])[NH:22][C@@H:23]1[CH2:24][C@H:25]([C:28](=[O:30])[N:7]([C:6]2[C:2]([Cl:1])=[N:3][N:4]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:5]=2)[CH3:8])[CH2:26][CH2:27]1)([CH3:16])([CH3:17])[CH3:18]

Participants

7

Reactant 3

HCID 79724-MethylmorpholineHCID 1512529(1S,3R)-3-(((tert-butoxy)carbonyl)amino)cyclopentane-1-carboxylic acidHCID 67499849HCID 67499849, compound

Product 1

HCID 131735115HCID 131735115, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-N-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.109 g, 0.523 mmol) and (1S,3R)-3-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (0.120 g, 0.523 mmol) in DMF (2.09 mL) was added 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl uronium hexafluorophosphate (HATU, 0.219 g, 0.576 mmol) to give a brown solution. To this solution was added 4-methylmorpholine (0.115 mL, 1.05 mmol). The reaction was stirred at room temperature overnight. The material was diluted with EtOAc and water. The organic layer was dried with MgSO4, filtered and concentrated to give orange oil, which was purified by silica gel chromatography eluting with EtOAc/hexanes provided the title compound F45 as an orange oil (0.100 g, 39%).

Workup

  1. customto give a brown solution
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give orange oil, which
  6. customwas purified by silica gel chromatography
  7. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-374a207c7edc495c989cf77efc01d874
Source dataset
uspto-grants-2016_03
Patent number
US09295260B2

Reaction notes

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